Cover Photo By: Allstate Arena House Photographer

After selling out 2 nights at Carol’s Pub in Chicago in February, Vincent Mason returned to the Windy City to do a free acoustic pop-up show at Bub City before opening up for Jordan Davis in the evening on the Ain’t Enough Road Tour. Reservations for tables were booked almost immediately, and some folks drove over 3 hours just for the chance to catch him in this intimate setting. The crowd waited over 90 minutes before Vincent finally took the stage for a five-song acoustic set that showcased his warm vocals and clever songwriting. Fans shouted out deep cuts, to which he jokingly responded, “I think I forgot all the words to that one,” drawing laughs from the crowd. Maybe not every fan got their request, but his charm certainly made up for it. After the set, he stuck around for a meet-and-greet, taking time to chat and snap selfies with everyone. Then, in true Chicago fashion, he raced the infamous rush-hour traffic to make it to Rosemont in time for soundcheck.

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The Ain’t Enough Road Tour has had my favorite lineup of the year. The show at Allstate Arena kicked off with Mackenzie Carpenter, whose set proved she’s one to watch. She performed tracks off her debut album Hey Country Queen, including “Only Girl” and “Dozen Red Flags.” Her sound is reminiscent of Megan Moroney which is no coincidence as Mackenzie has written several of Megan’s songs. Dressed in a stunning brown faux suede two-piece, she owned the stage like a seasoned headliner. She closed her high-energy set with “I Wish You Would,” her duet with Midland that’s climbing the charts all year.

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For his main set, Vincent Mason came out with a full band. While he kept a more grounded presence at center stage with his guitar, his stripped-back performance style worked to his advantage. His rich vocals and lyrical depth drew the crowd in. A standout moment came when he broke out the harmonica for “Train of Thought,” showcasing his versatility. He closed with his debut radio single, “Wish You Well”, which is a personal favorite of mine. Vincent Mason is quickly becoming a must-watch name in country music.

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Mitchell Tenpenny may be listed as an opener, but he’s a headliner in my book. Arguably one of the most underrated artists on the country music scene, Tenpenny had a hard time fitting all of his hits into a 40-minute set. He is authentic and original with his combo of punk rock and country blend. He performed some of his biggest hits like “Truth About You” and “We Got History.” I was ecstatic to see that he added “Bitches” back into his setlist. His ride or die fans sang every word of this deep cut. “Alcohol You Later” and “Drunk Me” still hit as hard as when he released them back in 2018. His discography is one to dive into. He closed with his cover of “Iris.” It's bittersweet knowing his two-year tour run with Jordan Davis is ending, but fans can look forward to seeing him hit the road with HARDY in 2026.

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Jordan Davis delivered exactly what you’d expect from an artist worthy of Entertainer of the Year consideration. With a deep discography and a steady stream of chart-toppers, his live show blends passion, energy, and authenticity. His Ain’t Enough Road album is easily one of the best country records of the year, and tracks like “Turn This Truck Around” translate perfectly on stage. He kept the setlist fresh with upbeat hits like “Almost Maybes” and “Singles You Up,” while also making space for emotional ballads like “Church in a Chevy.” While it was never a radio single, it still remains a powerful live moment.

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While raising a cup to cheers to the night, Jordan had a special message to the city of Chicago: “Here’s to the Chicago Cubs winning the World Series!” The Cubs, unfortunately, fell to the Milwaukee Brewers in Game 5 of the playoffs the next day, but it was wishful thinking. Another standout moment was bringing Mackenzie Carpenter back out to assist Davis with the duet “Mess with Missing You” that was originally recorded with Carly Pearce. Davis brought out his openers during the “mixtape” portion of his set, where a variety of songs from 2006 were sampled before closing with feel-good tracks “Buy Dirt” and “What My World Spins Around.”

For more information on Jordan Davis | For more information on Mitchell Tenpenny

For more information on Vincent Mason | For more information on Mackenzie Carpenter

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